Facile Synthesis of 3-Hydroxyglutamic Acids via Cyanation of Chiral N-Acyliminium Cation Derived from (S)-Malic Acid.
✍ Scribed by Makoto Oba; Atsushi Mita; Yoshinori Kondo; Kozaburo Nishiyama
- Publisher
- John Wiley and Sons
- Year
- 2006
- Weight
- 18 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0931-7597
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## Abstract Efficient syntheses of (+)‐__N__‐methylpseudoconhydrine (5) and (−)‐hydroxysedamine (10) are described starting from the readily available (2__RS,5S__)‐Methyl 5‐(__tert__‐butyldimethyl‐silyloxy)‐2‐ethoxypiperidine‐1‐carboxylate (1) and proceeding via homochiral acyliminium ion as an int
## Abstract The homochiral 1,3‐dioxanes 8a–e with a 2‐bromophenyl substituent in position 2 and an electrophilic group in position 4 were stereo‐ and regioselectively prepared from the (__S__)‐malic acid derivatives 6a, 6b, 11, and 14. Attempts to prepare the tricycles 5a–c by connecting the 2‐phen